Florida Keys Holiday Rentals
About Casai's Private Villas and Holiday Rentals in Florida Keys
Discover more than 14310 vacation rentals available in Florida Keys. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Florida Keys.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Florida Keys, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Florida Keys. On average, places to stay near Florida Keys offer 826.39 ft², with nightly prices averaging US $650.
With Casai, finding and comparing holiday rentals in Florida Keys is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Florida Keys
| Type | Count |
|---|---|
| Vacation Homes | 8686 |
| Holiday Apartments | 1261 |
| Villas | 379 |
| Cottages | 286 |
Use these Quick Filters to Find a Holiday Rental in Florida Keys
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Florida Keys.
Weather in Florida Keys, FL
View the weather forecast for Florida Keys before booking your Florida Keys Vacation Rentals to confirm your best time to go.
Top Attractions Around Florida Keys, FL
Casai offers a large selection of top attractions around Florida Keys . Research things to do on your vacation before you visit Florida Keys.
Other Places to Stay in Florida Keys, FL
Frequently Asked Questions About Florida Keys?
What are the top holiday rentals in Florida Keys?
With numerous options available in Florida Keys, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Florida Keys:
- Almond Tree Inn Hotel - Adults Only
- Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Oceanfront Key Largo Paradise~Private Beach~Pool~Tennis~Marina~Cafe/Bar
- Summer Fun Awaits! Clean and Cozy w TOP FLOOR VIEWS.Your Home Away From Home!
- Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
- Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec
- Key Lime Kottage- Waterfront Home on Gulf of Mexico w/Private Pool, Dock & More
- 🌴 Coco Plum Paradise 🌴 Private Bayfront Home Pool Hot Tub Dock View
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
How many holiday rentals have private pools in Florida Keys?
Discover a selection of holiday rentals with private pools near Florida Keys with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Island Time Escape - Charming Family Retreat
- Reel Key Largo Escape Ocean Pointe 5209
- Parking, Heated Pool, Pet Friendly - Seagate House
- "Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage
Which holiday homes in Florida Keys are best for families?
If you're searching for a family-friendly holiday home in Florida Keys, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Florida Keys:
- Oceanfront retreat with serene views & lanai U30
- Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025
- Parrot Perch by Avantstay Old Town Key West w/Shared Pool Month-long Stays Only
How many Casai.com holiday rentals are available in Florida Keys?
As of 2026, Casai boasts over 14310 properties listed in the Florida Keys area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Florida Keys.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Florida | 2225 |
| Old Town Vacation Rentals in Florida | 2199 |
| Downtown Vacation Rentals in Florida | 896 |
| Uptown - Upper Duval Vacation Rentals in Florida | 719 |
| Historic Seaport Vacation Rentals in Florida | 354 |
| Truman Annex Vacation Rentals in Florida | 328 |
| New Town Vacation Rentals in Florida | 103 |
| Bahama Village Vacation Rentals in Florida | 84 |
| Little Venice Vacation Rentals in Florida | 50 |
| Venetian Shores Vacation Rentals in Florida | 42 |
| Key Largo Village Vacation Rentals in Florida | 31 |
| Indigo Reef Marina Homes Vacation Rentals in Florida | 30 |
| Lower Matecumbe Beach Vacation Rentals in Florida | 24 |
| Pirates Cove Vacation Rentals in Florida | 1411 |
| Coral Lagoon Vacation Rentals in Florida | 1833 |
| Sunset Cove Vacation Rentals in Florida | 1403 |
